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932760

Sigma-Aldrich

3,4,9,10-Perylenetetracarboxylic dianhydride

Synonym(s):

PTCDA, Perylenetetracarboxylic acid dianhydride, Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224

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About This Item

Empirical Formula (Hill Notation):
C24H8O6
CAS Number:
Molecular Weight:
392.32
Beilstein:
57831
MDL number:
UNSPSC Code:
12352103
NACRES:
NA.21

Assay

99% (sublimed)

Quality Level

mp

>300 °C

solubility

DMSO: slightly soluble

Orbital energy

HOMO 5.85 eV 
LUMO 3.9 eV 

SMILES string

O1C(=O)c2c3c4c(c5c6c(c4cc2)ccc7c6c(cc5)C(=O)OC7=O)ccc3C1=O

InChI

1S/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H

InChI key

CLYVDMAATCIVBF-UHFFFAOYSA-N

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Application

3,4,9,10-Perylenetetracarboxylic dianhydride, also known as Perylenetetracarboxylic acid dianhydride, is a large π-conjugated semiconductor aromatic organic molecule. It is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments and dyes. It is a dark red solid with low solubility in aromatic solvents.
The compound has attracted much interest as an organic semiconductor. It has potential applications in organic and molecular electronics, and typically used as an archetype molecular compound. PTCDA shares many properties with conventional semiconductors (with their delocalized electronic states), and insulator-like organic molecular crystals (OMCs) (with their large absorption oscillator strengths, excitonic self-trapping, polaron-assisted conduction, etc.). That is due to extremely close π-π stacking, an unusually small intermolecular distance of only 3.21 A. Among its applications, it is important to highlight the latest focus on environment monitoring, self-assembly and photocatalysis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1


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